Phase Equilibria and Condensed Phase Properties of Fluorinated Alkanes via First Principles Simulations

Goel, Himanshu; Windom, Zachary W.; Butler, Charles L.; Rai, Neeraj

doi:10.1002/slct.201701972

Title: Phase Equilibria and Condensed Phase Properties of Fluorinated Alkanes via First Principles Simulations

Journal Article · 21 December 2017 · Chemistry Select

DOI: https://doi.org/10.1002/slct.201701972 · OSTI ID:1461756

Goel, Himanshu ^[1]; Windom, Zachary W. ^[1]; Butler, Charles L. ^[1];

^[1]

Mississippi State Univ., MS (United States). Dave C. Swalm School of Chemical Engineering and Center for Advanced Vehicular Systems

Vapor liquid equilibria (VLE) of organic compounds is governed by weak non-covalent interactions. This presents a significant challenge in predicting VLE using a first principles approach where density functional theory is used to model system potential. However, a dispersion corrected approach has significantly improved the performance of traditional density functionals. Here, we predict the VLE for a nonpolar carbon tetrafluoride (R14) and polar 1,1,1,2-tetrafluoroethane (R134a)via first principles Gibbs ensemble Monte Carlo simulations using PBED3 density functional. We find that the saturated liquid density for R14 is slightly under predicted for subcritical temperatures, while for R134a it is under predicted at lower reduced temperatures and over predicted at higher reduced temperatures. In the liquid phase, angle-resolved pair correlation functions indicate slight preference for R143a to align in parallel and antiparallel orientation in the first solvation shell.The vibrational spectra reveal peak broadening in the condensed phase due to solvothermal effects. Altogether, we find thePBED3 functional performance is better for the nonpolar molecule as compared to the polar one.

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Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States). National Energy Research Scientific Computing Center (NERSC)

Sponsoring Organization:: USDOE Office of Science (SC), Advanced Scientific Computing Research (ASCR)

Grant/Contract Number:: AC02-05CH11231; AC02-06CH11357

OSTI ID:: 1461756

Journal Information:: Chemistry Select, Vol. 2, Issue 36; ISSN 2365-6549

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 4 works

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References (76)

Cassandra: An open source Monte Carlo package for molecular simulation Shah, Jindal K.; Marin-Rimoldi, Eliseo; Mullen, Ryan Gotchy Journal of Computational Chemistry, Vol. 38, Issue 19 https://doi.org/10.1002/jcc.24807	journal	April 2017
Generalized Gradient Approximation Made Simple Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868 https://doi.org/10.1103/PhysRevLett.77.3865	journal	October 1996
Effective potentials for liquid simulation of the alternative refrigerants HFC-134a (CF3CH2F) and HFC-125 (CF3CHF2) Lísal, M.; Vacek, V. Fluid Phase Equilibria, Vol. 127, Issue 1-2 https://doi.org/10.1016/S0378-3812(96)03056-7	journal	January 1997
A multi-scale approach to characterize pure CH ₄ , CF ₄ , and CH ₄ /CF ₄ mixtures Chattoraj, Joyjit; Risthaus, Tobias; Rubner, Oliver The Journal of Chemical Physics, Vol. 142, Issue 16 https://doi.org/10.1063/1.4919079	journal	April 2015
High-pressure neutron diffraction on fluid carbon tetrafluoride and interpretation by reverse Monte Carlo simulations Waldner, I.; Bassen, A.; Bertagnolli, H. The Journal of Chemical Physics, Vol. 107, Issue 24 https://doi.org/10.1063/1.474183	journal	December 1997
HFC 134a as a substitute refrigerant for CFC 12 Spauschus, H. O. International Journal of Refrigeration, Vol. 11, Issue 6 https://doi.org/10.1016/0140-7007(88)90063-1	journal	November 1988
Microwave Spectroscopy of the Ground, ν18, 2ν18, and ν11Vibrational States of CF3CFH2 Ilyushin, V. V.; Alekseev, E. A.; Dyubko, S. F. Journal of Molecular Spectroscopy, Vol. 195, Issue 2 https://doi.org/10.1006/jmsp.1999.7825	journal	June 1999
Thermodynamic properties of two alternative refrigerants: 1,1-dichloro-2,2,2-trifluoroethane (R123) and 1,1,1,2-tetrafluoroethane (R134a) Morrison, Graham; Ward, David K. Fluid Phase Equilibria, Vol. 62, Issue 1-2 https://doi.org/10.1016/0378-3812(91)87006-U	journal	January 1991
Molecular Dynamics Studies on the Partially Miscible Binary Liquid Mixture Methane/Tetrafluoromethane Based on Lennard-Jones (12-6) Potentials Hoheisel, Claus Berichte der Bunsengesellschaft für physikalische Chemie, Vol. 81, Issue 5 https://doi.org/10.1002/bbpc.19770810504	journal	May 1977
Vapor–Liquid Coexistence Curves for Methanol and Methane Using Dispersion-Corrected Density Functional Theory McGrath, Matthew J.; Kuo, I. -F. Will; Ghogomu, Julius N. The Journal of Physical Chemistry B, Vol. 115, Issue 40 https://doi.org/10.1021/jp205072v	journal	October 2011
Infrared absorption cross sections for 1,1,1,2-tetrafluoroethane Harrison, Jeremy J. Journal of Quantitative Spectroscopy and Radiative Transfer, Vol. 151 https://doi.org/10.1016/j.jqsrt.2014.09.023	journal	January 2015
Configurational bias Monte Carlo: a new sampling scheme for flexible chains Siepmann, Jörn Ilja; Frenkel, Daan Molecular Physics, Vol. 75, Issue 1 https://doi.org/10.1080/00268979200100061	journal	January 1992
Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis Vosko, S. H.; Wilk, L.; Nusair, M. Canadian Journal of Physics, Vol. 58, Issue 8 https://doi.org/10.1139/p80-159	journal	August 1980
Microscopic structure of liquid 1-1-1-2-tetrafluoroethane (R134a) from Monte Carlo simulation Do, Hainam; Wheatley, Richard J.; Hirst, Jonathan D. Physical Chemistry Chemical Physics, Vol. 12, Issue 40 https://doi.org/10.1039/c0cp00620c	journal	January 2010
Rotational and Vibrational Spectroscopy and Ideal Gas Heat Capacity of HFC 134a (CF ₃ CFH ₂ ) Xu, Li-Hong; Andrews, Anne M.; Cavanagh, Richard R. The Journal of Physical Chemistry A, Vol. 101, Issue 12 https://doi.org/10.1021/jp9640383	journal	March 1997
Possible greenhouse effects of tetrafluoromethane and carbon dioxide emitted from aluminum production Weston, Ralph E. Atmospheric Environment, Vol. 30, Issue 16 https://doi.org/10.1016/1352-2310(95)00499-8	journal	August 1996
Maximally localized generalized Wannier functions for composite energy bands Marzari, Nicola; Vanderbilt, David Physical Review B, Vol. 56, Issue 20 https://doi.org/10.1103/PhysRevB.56.12847	journal	November 1997
Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen Dunning, Thom H. The Journal of Chemical Physics, Vol. 90, Issue 2 https://doi.org/10.1063/1.456153	journal	January 1989
Infrared and Raman spectra of fluorinated ethanes part XVIII. 1, 1, 1, 2-Tetrafluoroethane Rud Nielsen, J.; Halley, C. J. Journal of Molecular Spectroscopy, Vol. 17, Issue 2 https://doi.org/10.1016/0022-2852(65)90171-2	journal	August 1965
CH-Stretching Overtone Spectroscopy of 1,1,1,2-Tetrafluoroethane Saar, Brian G.; Steeves, Adam H.; Thoman, John W. The Journal of Physical Chemistry A, Vol. 109, Issue 24 https://doi.org/10.1021/jp058060k	journal	June 2005
HPFP, a Model Propellant for pMDIs Rogueda, Philippe G. A. Drug Development and Industrial Pharmacy, Vol. 29, Issue 1 https://doi.org/10.1081/DDC-120016682	journal	January 2003
Vapor–liquid equilibria of alternative refrigerants and their binaries by molecular simulations employing the reaction Gibbs ensemble Monte Carlo method Budinský, R.; Vacek, V.; Lı́sal, M. Fluid Phase Equilibria, Vol. 222-223 https://doi.org/10.1016/j.fluid.2004.06.047	journal	August 2004
Electron affinities of the first‐row atoms revisited. Systematic basis sets and wave functions Kendall, Rick A.; Dunning, Thom H.; Harrison, Robert J. The Journal of Chemical Physics, Vol. 96, Issue 9 https://doi.org/10.1063/1.462569	journal	May 1992
A review of uses, environmental hazards and recovery/recycle technologies of perfluorocarbons (PFCs) emissions from the semiconductor manufacturing processes Tsai, Wen-Tien; Chen, Horng-Ping; Hsien, Wu-Yuan Journal of Loss Prevention in the Process Industries, Vol. 15, Issue 2 https://doi.org/10.1016/S0950-4230(01)00067-5	journal	March 2002
Performance comparison between the combined R134a/CO 2 heat pump and cascade R134a/CO 2 heat pump for space heating Song, Yulong; Li, Dongzhe; Yang, Dongfang International Journal of Refrigeration, Vol. 74 https://doi.org/10.1016/j.ijrefrig.2016.12.001	journal	February 2017
Continuous Fractional Component Monte Carlo: An Adaptive Biasing Method for Open System Atomistic Simulations Shi, Wei; Maginn, Edward J. Journal of Chemical Theory and Computation, Vol. 3, Issue 4 https://doi.org/10.1021/ct7000039	journal	May 2007
Transferable Potentials for Phase Equilibria. 1. United-Atom Description of n-Alkanes Martin, Marcus G.; Siepmann, J. Ilja https://doi.org/10.1021/jp972543+		March 1998
Perfluoroalkanes: Conformational Analysis and Liquid-State Properties from ab Initio and Monte Carlo Calculations Watkins, Edward K.; Jorgensen, William L. The Journal of Physical Chemistry A, Vol. 105, Issue 16 https://doi.org/10.1021/jp004071w	journal	April 2001
The infrared and Raman spectra of CF3CH2I, CF3CH2Br, and CF3CH2F Edgell, Walter F.; Riethof, Thomas R.; Ward, Charlotte Journal of Molecular Spectroscopy, Vol. 11, Issue 1-6 https://doi.org/10.1016/0022-2852(63)90010-9	journal	January 1963
Experimental evaluation of a R134a/CO 2 cascade refrigeration plant Sanz-Kock, Carlos; Llopis, Rodrigo; Sánchez, Daniel Applied Thermal Engineering, Vol. 73, Issue 1 https://doi.org/10.1016/j.applthermaleng.2014.07.041	journal	December 2014
Investigation of Exchange Energy Density Functional Accuracy for Interacting Molecules Murray, Éamonn D.; Lee, Kyuho; Langreth, David C. Journal of Chemical Theory and Computation, Vol. 5, Issue 10 https://doi.org/10.1021/ct900365q	journal	August 2009
On the hydrogen bond nature of the C–H⋯F interactions in molecular crystals. An exhaustive investigation combining a crystallographic database search and ab initio theoretical calculations D'Oria, Emiliana; Novoa, Juan J. CrystEngComm, Vol. 10, Issue 4 https://doi.org/10.1039/b717276c	journal	January 2008
Exergy analysis of R413A as replacement of R12 in a domestic refrigeration system Padilla, Miguel; Revellin, Rémi; Bonjour, Jocelyn Energy Conversion and Management, Vol. 51, Issue 11 https://doi.org/10.1016/j.enconman.2010.03.013	journal	November 2010
Global warming potentials and radiative efficiencies of halocarbons and related compounds: A comprehensive review: HALOCARBON REVIEW Hodnebrog, Ø.; Etminan, M.; Fuglestvedt, J. S. Reviews of Geophysics, Vol. 51, Issue 2 https://doi.org/10.1002/rog.20013	journal	April 2013
Energy and environmental comparison of two-stage solutions for commercial refrigeration at low temperature: Fluids and systems Llopis, Rodrigo; Sánchez, Daniel; Sanz-Kock, Carlos Applied Energy, Vol. 138 https://doi.org/10.1016/j.apenergy.2014.10.069	journal	January 2015
Optimized density functionals from the extended G2 test set Schmider, Hartmut L.; Becke, Axel D. The Journal of Chemical Physics, Vol. 108, Issue 23 https://doi.org/10.1063/1.476438	journal	June 1998
Ideal gas thermodynamic properties of six fluoroethanes Chen, S. S.; Rodgers, A. S.; Choo, J. Journal of Physical and Chemical Reference Data, Vol. 4, Issue 2 https://doi.org/10.1063/1.555521	journal	April 1975
Absorption system based on the refrigerant R134a Borde, I.; Jelinek, M.; Daltrophe, N. C. International Journal of Refrigeration, Vol. 18, Issue 6 https://doi.org/10.1016/0140-7007(95)98161-D	journal	July 1995
Experimental Study of R134a, R406A and R600a Blends as Alternative To Freon 12 Akintunde, M. A., Akintunde, M. A. IOSR Journal of Mechanical and Civil Engineering, Vol. 7, Issue 1 https://doi.org/10.9790/1684-0714046	journal	January 2013
A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu Grimme, Stefan; Antony, Jens; Ehrlich, Stephan The Journal of Chemical Physics, Vol. 132, Issue 15 https://doi.org/10.1063/1.3382344	journal	April 2010
Simulating Fluid-Phase Equilibria of Water from First Principles ^† McGrath, Matthew J.; Siepmann, J. Ilja; Kuo, I-Feng W. The Journal of Physical Chemistry A, Vol. 110, Issue 2 https://doi.org/10.1021/jp0535947	journal	January 2006
Calculation of the Gibbs free energy of solvation and dissociation of HCl in water via Monte Carlo simulations and continuum solvation models McGrath, Matthew J.; Kuo, I-F. Will; Ngouana W., Brice F. Physical Chemistry Chemical Physics, Vol. 15, Issue 32 https://doi.org/10.1039/c3cp51762d	journal	January 2013
Molecular Simulation for Thermodynamic Properties and Process Modeling of Refrigerants Smith, William R.; Figueroa-Gerstenmaier, Susana; Skvorova, Magda Journal of Chemical & Engineering Data, Vol. 59, Issue 10 https://doi.org/10.1021/je500260d	journal	May 2014
An improved determination of the molecular dipole moment of HFC-134a: microwave Stark spectra and ab initio calculations Puzzarini, Cristina; Dore, Luca; Cludi, Lino Physical Chemistry Chemical Physics, Vol. 5, Issue 8 https://doi.org/10.1039/b300260h	journal	March 2003
Ab Initio Calculations of Vibrational Frequencies and Infrared Intensities for Global Warming Potential of CFC Substitutes: CF3CH2F (HFC-134a) Papasavva, Stella; Tai, Stephanie; Esslinger, Amy The Journal of Physical Chemistry, Vol. 99, Issue 11 https://doi.org/10.1021/j100011a006	journal	March 1995
Molecular simulation of the binary mixture of 1–1–1–2–tetrafluoroethane and carbon dioxide Do, Hainam; Wheatley, Richard J.; Hirst, Jonathan D. Physical Chemistry Chemical Physics, Vol. 13, Issue 34 https://doi.org/10.1039/c1cp21419e	journal	January 2011
Higher-accuracy van der Waals density functional Lee, Kyuho; Murray, Éamonn D.; Kong, Lingzhu Physical Review B, Vol. 82, Issue 8 https://doi.org/10.1103/PhysRevB.82.081101	journal	August 2010
High resolution FTIR spectroscopy of 1,1,1,2-tetrafluoroethane: Thompson, Christopher D.; Robertson, Evan G.; Evans, Corey J. Journal of Molecular Spectroscopy, Vol. 218, Issue 1 https://doi.org/10.1016/S0022-2852(02)00079-6	journal	March 2003
Liquid Water from First Principles: Investigation of Different Sampling Approaches Kuo, I-Feng W.; Mundy, Christopher J.; McGrath, Matthew J. The Journal of Physical Chemistry B, Vol. 108, Issue 34 https://doi.org/10.1021/jp047788i	journal	August 2004
First principles Monte Carlo simulations of aggregation in the vapor phase of hydrogen fluoride McGrath, Matthew J.; Ghogomu, Julius. N.; Mundy, Christopher J. Physical Chemistry Chemical Physics, Vol. 12, Issue 27 https://doi.org/10.1039/b924506e	journal	January 2010
Gibbs ensemble simulation of HCFC/HFC mixtures by effective Stockmayer potential Gao, G. T.; Wang, Wenchuan; Zeng, X. C. Fluid Phase Equilibria, Vol. 158-160 https://doi.org/10.1016/S0378-3812(99)00147-8	journal	June 1999
Vapour-liquid equilibria for dipolar two-centre Lennard-Jones fluids by Gibbs-Duhem integration Lísal, M.; Budinský, R.; Vacek, V. Fluid Phase Equilibria, Vol. 135, Issue 2 https://doi.org/10.1016/S0378-3812(97)00072-1	journal	August 1997
Density-functional approximation for the correlation energy of the inhomogeneous electron gas Perdew, John P. Physical Review B, Vol. 33, Issue 12 https://doi.org/10.1103/PhysRevB.33.8822	journal	June 1986
Phase equilibria by simulation in the Gibbs ensemble: Alternative derivation, generalization and application to mixture and membrane equilibria Panagiotopoulos, A. Z.; Quirke, N.; Stapleton, M. Molecular Physics, Vol. 63, Issue 4 https://doi.org/10.1080/00268978800100361	journal	March 1988
Transferable Potentials for Phase Equilibria. 9. Explicit Hydrogen Description of Benzene and Five-Membered and Six-Membered Heterocyclic Aromatic Compounds Rai, Neeraj; Siepmann, J. Ilja The Journal of Physical Chemistry B, Vol. 111, Issue 36 https://doi.org/10.1021/jp073586l	journal	September 2007
High-resolution IR spectroscopy of jet-cooled CF3CH2F McNaughton, Don; Evans, Corey; Robertson, Evan G. Journal of the Chemical Society, Faraday Transactions, Vol. 91, Issue 12 https://doi.org/10.1039/ft9959101723	journal	January 1995
Theoretical and experimental investigation of a combined R134a and transcritical CO2 heat pump for space heating Yang, Dongfang; Song, Yulong; Cao, Feng International Journal of Refrigeration, Vol. 72 https://doi.org/10.1016/j.ijrefrig.2016.07.016	journal	December 2016
Vapor Liquid Equilibria of Hydrofluorocarbons Using Dispersion-Corrected and Nonlocal Density Functionals Goel, Himanshu; Butler, Charles L.; Windom, Zachary W. Journal of Chemical Theory and Computation, Vol. 12, Issue 7 https://doi.org/10.1021/acs.jctc.6b00305	journal	June 2016
Microscopic and Thermodynamic Properties of the HFA134a−Water Interface: Atomistic Computer Simulations and Tensiometry under Pressure Peguin, Robson P. S.; Selvam, Parthiban; da Rocha, Sandro R. P. Langmuir, Vol. 22, Issue 21 https://doi.org/10.1021/la0608157	journal	October 2006
Accurate and simple analytic representation of the electron-gas correlation energy Perdew, John P.; Wang, Yue Physical Review B, Vol. 45, Issue 23, p. 13244-13249 https://doi.org/10.1103/PhysRevB.45.13244	journal	June 1992
Vibrational Fundamentals of CF ₃ CH ₂ X Molecules Harnish, D. F.; Hirschmann, R. P. Applied Spectroscopy, Vol. 24, Issue 1 https://doi.org/10.1366/000370270774372173	journal	January 1970
Resolution of the uncertainties in the radiative forcing of HFC-134a Forster, Piers M. de F.; Burkholder, J. B.; Clerbaux, C. Journal of Quantitative Spectroscopy and Radiative Transfer, Vol. 93, Issue 4 https://doi.org/10.1016/j.jqsrt.2004.08.038	journal	July 2005
Derivation of an Optimized Potential Model for Phase Equilibria (OPPE) for Sulfides and Thiols Delhommelle, J.; Tschirwitz, C.; Ungerer, P. The Journal of Physical Chemistry B, Vol. 104, Issue 19 https://doi.org/10.1021/jp994064b	journal	May 2000
Computing vibrational spectra from ab initio molecular dynamics Thomas, Martin; Brehm, Martin; Fligg, Reinhold Physical Chemistry Chemical Physics, Vol. 15, Issue 18 https://doi.org/10.1039/c3cp44302g	journal	January 2013
Predicting the Phase Equilibria of Mixtures of Hydrogen Fluoride with Water, Difluoromethane (HFC-32), and 1,1,1,2-Tetrafluoroethane (HFC-134a) Using a Simplified SAFT Approach Galindo, Amparo; Whitehead, Paul J.; Jackson, George The Journal of Physical Chemistry B, Vol. 101, Issue 11 https://doi.org/10.1021/jp962675n	journal	March 1997
Structural investigations of fluid carbon tetrafluoride by statistical mechanical calculations and Monte Carlo simulation Bassen, A.; Waldner, I.; Bertagnolli, H. Berichte der Bunsengesellschaft für physikalische Chemie, Vol. 102, Issue 4 https://doi.org/10.1002/bbpc.19981020404	journal	April 1998
Mie Potentials for Phase Equilibria Calculations: Application to Alkanes and Perfluoroalkanes Potoff, Jeffrey J.; Bernard-Brunel, Damien A. The Journal of Physical Chemistry B, Vol. 113, Issue 44 https://doi.org/10.1021/jp9072137	journal	November 2009
Development of an all-atoms force field from ab initio calculations for alternative refrigerants Fermeglia, Maurizio; Ferrone, Marco; Pricl, Sabrina Fluid Phase Equilibria, Vol. 210, Issue 1 https://doi.org/10.1016/S0378-3812(03)00165-1	journal	July 2003
Left-right correlation energy Handy, Nicholas C.; Cohen, Aron J. Molecular Physics, Vol. 99, Issue 5 https://doi.org/10.1080/00268970010018431	journal	March 2001
A study of solid and liquid carbon tetrafluoride using the constant pressure molecular dynamics technique Nosé, Shuichi; Klein, Michael L. The Journal of Chemical Physics, Vol. 78, Issue 11 https://doi.org/10.1063/1.444641	journal	June 1983
Infrared band strengths of HFC-134a vapour Newnham, D.; Ballard, J.; Page, M. Journal of Quantitative Spectroscopy and Radiative Transfer, Vol. 55, Issue 3 https://doi.org/10.1016/0022-4073(95)00164-6	journal	March 1996
Theoretical investigation on the combined and cascade CO2/R134a heat pump systems for space heating Song, Yulong; Li, Dongzhe; Cao, Feng Applied Thermal Engineering, Vol. 124 https://doi.org/10.1016/j.applthermaleng.2017.06.014	journal	September 2017
Prediction of Phase Equilibria for Refrigerant Mixtures of Difluoromethane (HFC-32), 1,1,1,2-Tetrafluoroethane (HFC-134a), and Pentafluoroethane (HFC-125a) Using SAFT-VR Galindo, Amparo; Gil-Villegas, Alejandro; Whitehead, Paul J. The Journal of Physical Chemistry B, Vol. 102, Issue 39 https://doi.org/10.1021/jp9809437	journal	September 1998
Nonlocal van der Waals Density Functional Made Simple Vydrov, Oleg A.; Van Voorhis, Troy Physical Review Letters, Vol. 103, Issue 6 https://doi.org/10.1103/PhysRevLett.103.063004	journal	August 2009
Vapor–liquid equilibria of water from first principles: comparison of density functionals and basis sets McGrath, M. J.; Siepmann, J. I.; Kuo, I. -F. W. Molecular Physics, Vol. 104, Issue 22-24 https://doi.org/10.1080/00268970601014781	journal	November 2006
All-Atom Force Field for the Prediction of Vapor−Liquid Equilibria and Interfacial Properties of HFA134a Peguin, Robson P. S.; Kamath, Ganesh; Potoff, Jeffrey J. The Journal of Physical Chemistry B, Vol. 113, Issue 1 https://doi.org/10.1021/jp806213w	journal	January 2009